Councillor Kristyn Wong-Tam and the homophobic letter she received last week on the Day of Pink. Photo via Twitter.

The failed political candidate, leader of the New Constitution Party, editor of Your Ward News, and self-proclaimed “faith healer,” “precision belly rubber,” and “expert at shaming people into doing the right thing,” Dr. James Sears is back in the news, and many are questioning if he has any connection to a homophobic letter sent to the office of Councillor Kristyn Wong-Tam (Ward 27, Toronto Centre-Rosedale).

Last week, on the Day of Pink, Wong-Tam received a letter that began, “I support Mr. William Whatcott crusade 100% I stand with millions of people to shut you—” and then it proceeds—in just eight lines—to use six separate racial and homophobic epithets. The letter, on its own, is horrific. What’s curious, though, is the return address on the outside of the envelope: 163 Main Strreet—the office of the neo-Nazi “newspaper“ called “Your Ward News,” run by Leroy St. Germaine and the infamous James Sears, also known as Dimitri the Lover (his pickup artist name).

Sears claims, in an email, that the letter was a “hate mail hoax” designed to discredit his (already thoroughly discredited) “newspaper” ahead of a hearing to determine whether it will remain banned from being delivered by Canada Post. But, then of course, if you’re James Sears, why stop there? “Furthermore,” Sears continues, “the fact that Councillor Wong-Tam published the letter’s return address rather than wait for police to review the matter, makes me suspect that either she is complicit in the hoax, or she saw an opportunity to use it for political theatre.”

The possible involvement with the hate mail, his career as a self-declared “love guru,” and his “newspaper” are bad enough, but they only barely scratch the surface of James Nicholas Sears.

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Sears graduated from the University of Toronto’s medical school in 1988. Despite the fact that, as an intern, he was noted to have skipped his duties, drank on the job, and abused prescription drugs, he was deemed “competent for unsupervised practice.”Within three years, he had been charged with sexual assault relating to his medical practice. According to court documents, while working for Medvisit Doctor’s House Service in Ottawa, Sears, on more than one occasion, complained about his wife’s lack of interest in sex to patients, telling one that he “could do it 10 times a day,” and masturbating in a patient’s bathroom shortly thereafter.

In 1994, Sears started the Second Opinion Medical-Legal Consultants Group—a company that offered “medical investigative services.” (Sears claimed that he was “the world’s top Medical Investigator” and had operated in over 40 countries.) Despite Sears’s sordid past, Second Opinion was somewhat successful: in 2001, it was reported in the Starthat they had been hired at one point by both Canadian Tire and the Toronto Transit Commission.

Around 2005, Sears began referring to himself as “Dimitri” and created DimitriTheLover.com in 2006. Shortly after, he founded Toronto Real Men, a pickup artistry business that claimed to be the world’s “first and only seduction lair.” ([Ron Howard Narrating Arrested Development voice]: It wasn’t.) In 2008, Torontoist dubbed him the number two villain in Toronto, and he became a minor laughing stock of the internet when a series of deranged voicemails he had left were posted online:

[WARNING: AUDIO CONTAINS POTENTIALLY UPSETTING MATERIAL]

Sears is also involved in the fringes of the mortgage industry. In 2005, he claimed to be the owner of Trillium Mortgages in an article published in Canadian Business.

However, a source who has worked with Sears (who requested that their name not be printed), who I spoke with in late 2015, contradicted the claim, saying that Sears was simply an employee. The source described his bizarre “penchant for sex” and erratic behaviour. “He’s crazy, he’s just nuts,” the source said. “This guy’s a sociopath.” In 2008, his application for a mortgage broker’s license was denied, but sources told me that as of late 2015 he was continuing to work at Expert Mortgage Company—which, on its website, advertises the services of a “full-time in-house marketing guru”:

Screengrab from expertmortgagebrokers.ca

While it’s not been verified that Sears is, in fact, the “full-time in-house marketing guru,” two things jump out: the first is that “guru” is a word that Sears uses often, and second that on his 2014 council campaign website (Sears ran against Ward 32 Councillor Mary-Margaret McMahon, in spectacularly heinous fashion), he described himself as “Ontario’s #1 Trainer of Sales Consultants, with Specialization in Mortgage & Real Estate Agents.” Some of Expert Mortgages’ public material shares Sears’s blame-others approach to failure: new agents at Expert Mortgages, for instance, are asked to pay a $1,000 “ineptitude deposit,” to insure against the possibility that,“If you cannot close a deal within the first 12 months of employment with us, then obviously you are either putting forth zero effort or you are not obeying our instructions. Under those very rare circumstances you will forfeit your deposit for wasting our valuable time training and supporting you.”

Sears’s involvement in the financial services industry, though, may explain his financial strength. Sears has financed his political endeavours entirely independently, putting up staggering figures for campaigns that were destined to fail. When he ran for Toronto City Council in 2014, Sears financed his campaign, according to candidate financial records available from the City, entirely independently, putting up over $35,000 of his own funds. He has also put up big numbers to fund his federal election campaign: on September 15, 2015, Sears announced via Twitter that he had secured $75,000 to fund his campaign. (This may not be entirely true: federal candidate campaign financial documents show that his campaign only ever received approximately half that amount. As well, $3,000 of the approximately $35,000 he spent during the campaign was funnelled towards his own “newspaper.”)

Sears, when provided with an opportunity to comment, responded: “You are still banned from asking me questions. DO NOT CONTACT ME AGAIN!” [sic]

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That hate mail made its way to Wong-Tam’s office with a return address connected to Your Ward News is not surprising, given that the “newspaper” is as close to the leading voice that the Toronto neo-Nazi community has. There’s also no way to confidently determine the identity of the person who wrote the letter.

But there’s a bigger point to consider in all of this: as evidenced by raucous white supremacyrallies hosted by more prominent media figures like Ezra Levant, there’s an ascendant extreme right that exists in Toronto. What you can take away from the example of James Sears and the letter sent to Wong-Tam is that this is not nearly as fringe as we would like to believe. It rears its head in ugly Rebel Media rallies, but lives and breathes off smaller organizations and operate through community newspapers, political campaigns, and mortgage brokerage firms. Anonymous hate mail, like the letter that Wong-Tam received last week, is deeply unsatisfying, mostly because you are powerless to respond to it. The author of the letter may, or may not, be connected to Your Ward News and James Sears in any official capacity, but regardless, it is an important reminder that white supremacy cannot be permitted to go on unacknowledged.

The letter was received on April 12, the Day of Pink—a day organized by the Canadian Centre for Gender & Sexual Diversity. It is a visible reminder that these organizations need support. For more information, click here.